Ethyl 2-bromo-1,3-thiazole-4-carboxylate → 1-{2-[4-((trans)-Octahydro-isoquinoline-2-carbonyl)-thiazol-2-yl]-phenyl}-ethanone

HRID 1990995Notes

Reaction equation

HRID 1990995 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)(=[O:3])[CH3:2].C(O[C:16]([C:18]1[N:19]=[C:20](Br)[S:21][CH:22]=1)=[O:17])C.[NH:24]1[C@H:33]2[C@@H:28]([CH2:29][CH2:30][CH2:31][CH2:32]2)[CH2:27][CH2:26][CH2:25]1>>[CH2:33]1[C@H:28]2[C@@H:27]([CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:26][CH2:25][N:24]1[C:16]([C:18]1[N:19]=[C:20]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:1](=[O:3])[CH3:2])[S:21][CH:22]=1)=[O:17]

Participants

4

Reactant 3

HCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 27343092-Acetylphenylboronic acidHCID 6994352(4aS,8aR)-Decahydroquinoline

Product 1

HCID 866136751-{2-[4-((trans)-Octahydro-isoquinoline-2-carbonyl)-thiazol-2-yl]-phenyl}-ethanone

Procedure

1-{2-[4-((trans)-Octahydro-isoquinoline-2-carbonyl)-thiazol-2-yl]-phenyl}-ethanone was synthesized in a similar manner, by the reaction of 2-acetyl-phenyl-boronic acid (Aldrich) with 2-bromo-thiazole-4-carboxylic acid ethyl ester (Combi-Blocks, Inc., San Diego, Calif.) in a Suzuki reaction, followed by hydrolysis and coupling with trans-decahydroquinoline.

Sources & evidence

ORD record
ord-23b1920e62ef403eb12f049b49f9b2f3
Source dataset
uspto-grants-2010_01
Patent number
US07645773B2

Reaction notes

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