5-Cyanothiophene-2-boronic acid → HCID 178454011, compound

HRID 2271691Notes

Reaction equation

HRID 2271691 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13])=[C:5]2[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.[C:32]([C:34]1[S:38][C:37](B(O)O)=[CH:36][CH:35]=1)#[N:33]>>[C:32]([C:34]1[S:38][C:37]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12]([CH:14]2[CH2:15][CH2:16]2)=[O:13])=[C:5]3[NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:20][CH2:19]2)=[CH:36][CH:35]=1)#[N:33]

Participants

3

Reactant 2

HCID 41987435-Cyanothiophene-2-boronic acidHCID 178454009HCID 178454009, compound

Product 1

HCID 178454011HCID 178454011, compoundYield 47%

Procedure

Following general procedure D, tert-butyl trans-4-[6-bromo-3-(cyclopropanecarbonyl)quinolin-4-ylamino]cyclohexylcarbamate (49 mg, 0.100 mmol) was reacted with 5-cyanothiophen-2-ylboronic acid (31 mg, 0.200 mmol) to afford the desired product (24 mg, 47%) as a brown solid: ESI MS m/z 517 [C29H32N4O3S+H]+.

Sources & evidence

ORD record
ord-ffd221b4c9dd4b96be78df0b367ad8a6
Source dataset
uspto-grants-2015_09
Patent number
US09120749B2

Reaction notes

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