tert-Butyl acrylate → 1-ethyl-3-(methylaminomethyl)-1H-indole

HRID 1361963Notes

Reaction equation

HRID 1361963 reaction equation
C(OC(C)(C)C)(=O)C=C.C(O[C:18]([N:20]([CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]([CH:32](C)[CH3:33])[CH:24]=1)C)=O)C1C=CC=CC=1.C(OC(N(CC1C2C(=CC=CC=2)N(CC2C=CC=CC=2)C=1)C)=O)C1C=CC=CC=1>>[CH2:32]([N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]([CH2:22][NH:20][CH3:18])=[CH:24]1)[CH3:33]

Participants

4

Reactant 3

HCID 15458tert-Butyl acrylateHCID 221390153-[N-(Benzyloxycarbonyl)-N-methylaminomethyl)-1-benzyl-1H-indoleHCID 221390783-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-isopropyl-1H-indole

Product 1

HCID 221391011-ethyl-3-(methylaminomethyl)-1H-indoleYield 87.3%

Procedure

According to the procedure of Preparation 17 (c), except substituting 3-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-isopropyl-1H-indole (0.99 g, 2.98 mmole) for the 3-[N-(Benzyloxycarbonyl)-N-methylaminomethyl]-1-benzyl-1H-indole, the title compound (0.49 g, 82%) was prepared as a white solid: MS (ES) ml/e 405 (2M+H)+.

Sources & evidence

ORD record
ord-748bc235fd5d43618fbfc8326717c7ff
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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