4-Bromoisoquinoline → tert-Butyl 4-(isoquinolin-4-yl)phenylcarbamate

HRID 1405065Notes

Reaction equation

HRID 1405065 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[C:12]([O:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].CC1C=CN=CC=1C1C=CC=C2C=1C=NN2>>[CH:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:17](=[O:18])[O:16][C:12]([CH3:14])([CH3:13])[CH3:15])=[CH:25][CH:24]=2)=[CH:3][N:4]=1

Participants

4

Reactant 3

HCID 737434-BromoisoquinolineHCID 3613184(4-Boc-Aminophenyl)Boronic AcidHCID 667156544-(4-methylpyridin-3-yl)-1H-indazole

Product 1

HCID 68086489tert-Butyl 4-(isoquinolin-4-yl)phenylcarbamate

Procedure

Intermediate 10A was prepared from 4-bromoisoquinoline and 4-(tert-butoxy carbonylamino)phenylboronic acid by the procedure described for the preparation of Intermediate 1C, and was obtained as an off-white foam (63% yield). MS (ES): m/z=321.2 [M+H]+. HPLC Ret timea: 2.432 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (s, 9 H) 7.44 (d, J=8.53 Hz, 2 H) 7.65 (d, J=8.53 Hz, 2 H) 7.68-7.75 (m, 1 H) 7.75-7.82 (m, 1 H) 7.88 (d, J=8.53 Hz, 1 H) 8.20 (d, J=7.78 Hz, 1 H) 8.40 (s, 1 H) 9.31 (s, 1 H) 9.57 (s, 1 H).

Sources & evidence

ORD record
ord-0ab912ddae0041caacc8493fad93e1a9
Source dataset
uspto-grants-2014_12
Patent number
US08916553B2

Reaction notes

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