4-(Tert-butyl)cinnamic acid → (2E)-3-[4-(tert-Butyl)phenyl]-N-[1-(2-hydroxyethyl)indol-6-yl]prop-2-enamide

HRID 2105580Notes

Reaction equation

HRID 2105580 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][N:22]3[CH2:25][CH2:26][O:27][Si](C)(C)C(C)(C)C)=[CH:18][CH:17]=2)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(/C=C/C(O)=O)=CC=1)(C)(C)C.C[Si](C)(OCCN1C2C(=CC=C(N)C=2)C=C1)C(C)(C)C>>[C:1]([C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][N:22]3[CH2:25][CH2:26][OH:27])=[CH:18][CH:17]=2)=[O:14])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 7248394-(Tert-butyl)cinnamic acidHCID 57808151(2E)-3-[4-(tert-Butyl)phenyl]-N-{1-[2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl]indol-6-yl}prop-2-enamideHCID 578081911-[2-(1,1,2,2-Tetramethyl-1-silapropoxy)ethyl]indole-6-ylamine

Product 1

HCID 10126176(2E)-3-[4-(tert-Butyl)phenyl]-N-[1-(2-hydroxyethyl)indol-6-yl]prop-2-enamide

Procedure

(2E)-3-[4-(tert-Butyl)phenyl]-N-{1-[2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl]indol-6-yl}prop-2-enamide. Analogous to the procedure used to prepare Example 1, 4-tert-butyl-trans-cinnamic acid (200 mg, 1.0 mmol, EMKA-Chemie) and 1-[2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl]indole-6-ylamine, Example 72(a), (290 mg, 1.0 mmol) provided the title product. MS (ESI, pos. ion) m/z: 477 (M+1).

Sources & evidence

ORD record
ord-7cacfb8544344a9ba7577486182b9d69
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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