HCID 50999229, compound → (2E)-3-[6-(tert-Butyl)(3-pyridyl)]-N-[1-(2-hydroxyethyl)indol-5-yl]prop-2-enamide

HRID 730284Notes

Reaction equation

HRID 730284 reaction equation
[C:1]([C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][CH2:26][O:27][Si](C)(C)C(C)(C)C)[CH:20]=[CH:19]3)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=CC(/C=C/C(O)=O)=CC=1)(C)(C)C.C[Si](C)(OCCN1C2C(=CC(N)=CC=2)C=C1)C(C)(C)C>>[C:1]([C:5]1[N:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]3)=[O:14])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 50999229HCID 50999229, compoundHCID 57807969(2E)-3-[6-(tert-butyl)(3-pyridyl)]-N-{1-[2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl]indol-5-yl}prop-2-enamideHCID 578083091-[2-(1,1,2,2-Tetramethyl-1-silapropoxy)ethyl]indole-5-ylamine

Product 1

HCID 10309141(2E)-3-[6-(tert-Butyl)(3-pyridyl)]-N-[1-(2-hydroxyethyl)indol-5-yl]prop-2-enamide

Procedure

(2E)-3-[6-(tert-butyl)(3-pyridyl)]-N-{1-[2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl]indol-5-yl}prop-2-enamide. Analogous to the procedure used to prepare Example 1, (2E)-3-[6-(tert-butyl)(3-pyridyl)]prop-2-enoic acid, Example 44(b), (41 mg, 0.20 mmol) and 1-[2-(1,1,2,2-tetramethyl-1-silapropoxy)ethyl]indole-5-ylamine, Example 73(a), (60 mg, 0.20 mmol) provided the title product. MS (ESI, pos. ion) m/z: 478 (M+1).

Sources & evidence

ORD record
ord-cfce4c07f7b441f7af744ca5a88c3601
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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