Sodium ethoxide → 5-(3-Ethanesulfonyl-phenyl)-8-ethoxy-3-methyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole

HRID 1642525Notes

Reaction equation

HRID 1642525 reaction equation
Cl[C:2]1[C:7]2[NH:8][C:9]3[C:14]([C:6]=2[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])[CH:17]=2)=[CH:4][N:3]=1)=[CH:13][C:12]([CH3:15])=[CH:11][N:10]=3.[O-:27][CH2:28][CH3:29].[Na+]>C(O)C>[CH2:25]([S:22]([C:18]1[CH:17]=[C:16]([C:5]2[C:6]3[C:14]4[CH:13]=[C:12]([CH3:15])[CH:11]=[N:10][C:9]=4[NH:8][C:7]=3[C:2]([O:27][CH2:28][CH3:29])=[N:3][CH:4]=2)[CH:21]=[CH:20][CH:19]=1)(=[O:24])=[O:23])[CH3:26]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 161232148-Chloro-5-(3-ethanesulfonyl-phenyl)-3-methyl-9H-dipyrido[2,3-b; 4',3'-d]pyrrole

Product 1

HCID 161233245-(3-Ethanesulfonyl-phenyl)-8-ethoxy-3-methyl-9H-dipyrido[2,3-b;4',3'-d]pyrroleYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 32 (4 mg, 0.01 mmol) was heated in a solution of sodium ethoxide in ethanol (21 wt. %, 0.5 mL) at 200° C. in the microwave for 30 min. Purification by prep-HPLC gave 3.2 mg (78%) of the title compound as a pale yellow solid. 1H NMR (400 MHz, MeOD-d4): δ 8.47 (br s, 1H), 8.18 (s, 1H), 8.03 (d, 1H, J=7.6 Hz), 7.96 (d, 1H, J=7.6 Hz), 7.81-7.89 (m, 3H), 4.63 (q, 2H, J=7.2 Hz), 3.26 (q, 2H, J=7.2 Hz), 2.38 (s, 3H), 1.56 (t, 3H, J=7.6 Hz), 1.32 (t, 3H, J=7.6 Hz). MS (ES) [m+H] calc'd for C21H21N3O3S, 396; found 396.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-b6a0a95ff9b1439e90436ba3380ef743
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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