4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

Base Information

Chemical Name:4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester
CAS No.:157425-66-6
Molecular Formula:C₂₁H₂₀N₂O₆
Molecular Weight:396.4
Hs Code.:

Synonyms:4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

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Chemical Property of 4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

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Technology Process of 4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

There total 13 articles about 4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

: 4-Hydroxy-8-oxo-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

: 157425-66-6
4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; at -20 ℃; for 0.333333h;
DOI:10.1248/cpb.44.67

Reference yield:

: trans-(+/-)-5-acetoxy-1-(benzyloxycarbonyl)-2-<2-<3-bromo-5-(methoxycarbonyl)-1H-pyrrol-2-yl>-2-oxoethyl>-1,2,5,6-tetrahydro-5-hydroxypyridine

: 157425-66-6
4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 93 percent / 1.5 percent K₂CO₃ / methanol / 2 h / 19 °C

2: 72 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / a) 0 deg C, 20 min, b) 20 deg C, 3 h

3: 11 percent / Pd(OAc)2, (o-tol)3P, Et₃N / acetonitrile / 26 h / 110 °C

4: 76 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / a) -20 deg C, 2 h, b) 0 deg C, 1.5 h

5: Et₃N / CH₂Cl₂ / a) 0 deg C, 10 min, b) 22 deg C, 1.5 h

6: 1 N Bu₄NF / tetrahydrofuran / 13 h / 0 - 22 °C

7: 21 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 - -10 °C

8: 24 mg / p-TsOH*H₂O / acetone / 2.5 h / 24 °C

9: 79 percent / NaBH₄ / methanol / 0.33 h / -20 °C

With palladium diacetate; sodium tetrahydroborate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; tris-(o-tolyl)phosphine; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; acetonitrile;
DOI:10.1248/cpb.44.67

Reference yield:

: cis-(+/-)-1-(benzyloxycarbonyl)-2-<2-<3-bromo-5-(methoxycarbonyl)-1H-pyrrol-2-yl>-2-oxoethyl>-1,2,5,6-tetrahydro-5-hydroxypyridine

: 157425-66-6
4,8-Dihydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid 6-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 74 percent / diethyl azodicarboxylate, Ph₃P / tetrahydrofuran / 1.5 h / 22 °C

2: 93 percent / 1.5 percent K₂CO₃ / methanol / 2 h / 19 °C

3: 72 percent / trifluoromethanesulfonic acid / cyclohexane; CH₂Cl₂ / a) 0 deg C, 20 min, b) 20 deg C, 3 h

4: 11 percent / Pd(OAc)2, (o-tol)3P, Et₃N / acetonitrile / 26 h / 110 °C

5: 76 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / a) -20 deg C, 2 h, b) 0 deg C, 1.5 h

6: Et₃N / CH₂Cl₂ / a) 0 deg C, 10 min, b) 22 deg C, 1.5 h

7: 1 N Bu₄NF / tetrahydrofuran / 13 h / 0 - 22 °C

8: 21 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 - -10 °C

9: 24 mg / p-TsOH*H₂O / acetone / 2.5 h / 24 °C

10: 79 percent / NaBH₄ / methanol / 0.33 h / -20 °C

With palladium diacetate; sodium tetrahydroborate; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; tris-(o-tolyl)phosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; acetonitrile;
DOI:10.1248/cpb.44.67