(4-Methoxyphenyl)boronic acid → HCID 70133754, compound

HRID 1531319Notes

Reaction equation

HRID 1531319 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C:18]([NH2:38])([CH2:23][C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:27]=3)[C:19]([O:21]C)=[O:20])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.COC1C=CC(B(O)O)=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([C:18]([NH2:38])([CH2:23][C:24]#[C:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH:27]=3)[C:19]([OH:21])=[O:20])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 70139422HCID 70139422, compound

Product 1

HCID 70133754HCID 70133754, compound

Procedure

Methyl 2-{[4′-methoxy-(1,1′-biphenyl)-4-yl]-sulfonyl}-amino-5-(3-morpholino-phenyl)-pent-4-ynoate: The starting sulfonamide 5b (367 mg, 0.66 mmol) is converted to the title compound with 4-methoxyphenylboronic acid (151 mg. 1.14 mmol) as described. for compound 3b. The crude product is adsorbed onto silica and then eluted through a column of flash silica with Hexanes:EtOAc (4:1 to 1:1) to give a pale orange-yellow, foamy solid.

Sources & evidence

ORD record
ord-95cb99fc51c94afca8a46d8ac20c3430
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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