Phenylboronic Acid → (S)-3-(2-phenyl-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester

HRID 716513Notes

Reaction equation

HRID 716513 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1[C:14](=[O:25])[NH:15][C:16]1[N:17]=[C:18]2[N:22]([CH:23]=1)[CH:21]=[C:20](Br)[S:19]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@H:9]1[C:14](=[O:25])[NH:15][C:16]1[N:17]=[C:18]2[N:22]([CH:23]=1)[CH:21]=[C:20]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:19]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 66827Phenylboronic AcidHCID 67240885(S)-3-(2-bromo-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 67241216(S)-3-(2-phenyl-imidazo[2,1-b]thiazol-6-ylcarbamoyl)-morpholine-4-carboxylic acid tert-butyl ester

Procedure

Compound 15 was synthesized from compound 14 (0.155 mmol) and phenylboronic acid (0.492 mmol), following the procedure as described for compound A1 to give compound 15 as a yellow gum in 38% yield. MS (ESI, EI+) m/z=429 (MH+).

Sources & evidence

ORD record
ord-bb0bdef7267846c98f505f8c9d069279
Source dataset
uspto-grants-2015_11
Patent number
US09187496B2

Reaction notes

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