Quinoline-3-boronic acid → 2-(4-Hydroxycyclohexylamino)-4-(1-(quinolin-3-yl)isoquinolin-5-yl)benzamide
Reaction equation
N1C2C(=CC=CC=2)C=C(B(O)[OH:12])C=1.Br[C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][N:19]=[C:20]2[C:25]1[CH:26]=[N:27][C:28]2[C:33]([CH:34]=1)=[CH:32][CH:31]=[CH:30][CH:29]=2.[C:35]([C:37]1[CH:42]=[CH:41][C:40](B2OC(C)(C)C(C)(C)O2)=[CH:39][C:38]=1[NH:52][CH:53]1[CH2:58][CH2:57][CH:56]([OH:59])[CH2:55][CH2:54]1)#[N:36]>>[OH:59][CH:56]1[CH2:57][CH2:58][CH:53]([NH:52][C:38]2[CH:39]=[C:40]([C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH:17]=[CH:18][N:19]=[C:20]4[C:25]3[CH:26]=[N:27][C:28]4[C:33]([CH:34]=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:41]=[CH:42][C:37]=2[C:35]([NH2:36])=[O:12])[CH2:54][CH2:55]1Participants
4
Procedure
3-(5-Bromoisoquinolin-1-yl)quinoline was obtained according to Example 2(1) using 3-quinolineboronic acid instead of 4-cyano-3-(4-hydroxycyclohexylamino)phenylboronic acid pinacol ester. A compound of Comparative Example 1 was obtained as a pale yellow solid (yield based on 3 steps: 24%) according to Example 2(3) using the obtained 3-(5-bromoisoquinolin-1-yl)quinoline instead of compound (2b) and 4-cyano-3-(4-hydroxycyclohexylamino)phenylboronic acid pinacol ester instead of 4-cyano-3-(ethylamino)phenylboronic acid pinacol ester.
Workup
- customA compound of Comparative Example 1 was obtained as a pale yellow solid (yield based on 3 steps: 24%)
Sources & evidence
- ORD record
- ord-1f288c0c2d5f44958d222905224ffde5
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912181B2
Reaction notes
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