N,N-dimethyl-4-phenylmethoxybenzamide → 4-(4-Benzyloxybenzoyl)-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine

HRID 1422099Notes

Reaction equation

HRID 1422099 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=13)[C:6]([CH2:13][CH3:14])=[C:5]2[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.C([Li])(C)(C)C.CN(C)[C:30](=[O:45])[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:33][CH:32]=1>>[CH2:38]([O:37][C:34]1[CH:33]=[CH:32][C:31]([C:30]([C:2]2[CH:3]=[C:4]3[N:12]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=24)[C:6]([CH2:13][CH3:14])=[C:5]3[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:45])=[CH:36][CH:35]=1)[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 2995264N,N-dimethyl-4-phenylmethoxybenzamideHCID 187069394-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizineHCID 178418306HCID 178418306, compound

Product 1

HCID 187069884-(4-Benzyloxybenzoyl)-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizineYield 14%

Procedure

4-Bromo-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine, prepared in example 75, step 2, was reacted with t-butyllithium and N,N-dimethyl 4-benzyloxybenzamide by the general synthetic principles outlined in example 75, to afford 4-(4-benzyloxybenzoyl)-1-ethyl-2-(4-methoxyphenyl)pyrrolo[2,1,5-cd]indolizine in 14% yield. MS(SP): m/z 485 (M+). 1H--NMR (CDCl3, 200 MHz) δ: 1.48 (t, 3 H); 3.21 (q, 2 H); 3.90 (s, 3 H); 5.17 (s, 2 H); 7.03-7.12 (m,4 H); 7.30-7.50 (m, 5 H); 7.70 (d, 2 H); 7.80-8.01 (m, 5 H); 8.39 (dd, 1 H).

Sources & evidence

ORD record
ord-2a4d81568e99457d926801380b0ccc58
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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