3-Bromoquinoline → Tert-butyl methyl(4-(quinolin-3-yl)phenyl)carbamate

HRID 452318Notes

Reaction equation

HRID 452318 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:12][N:13]([C:21]1[CH:26]=[CH:25][C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17]>>[CH3:12][N:13]([C:21]1[CH:26]=[CH:25][C:24]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:23][CH:22]=1)[C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:17])[CH3:18]

Participants

3

Reactant 2

HCID 214133-BromoquinolineHCID 4712653tert-Butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Product 1

HCID 66700372Tert-butyl methyl(4-(quinolin-3-yl)phenyl)carbamate

Procedure

3-Bromoquinoline (42 mg, 0.2 mmol) and tert-butyl methyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (66 mg, 0.2 mmol) were reacted using General Procedure (A) to afford tert-butyl methyl(4-(quinolin-3-yl)phenyl)carbamate a clear wax (44 mg, 66%). 1H NMR (400 MHz, CDCl3): δ 9.18 (d, J=2.4 Hz, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.15 (m, 1H), 7.89 (m, 1H), 7.73 (m, 1H), 7.68 (m, 2H), 7.59 (m, 1H), 7.42 (m, 2H), 3.3 (s, 3H), 1.50 (s, 9H); MS (ESI): 335 (M+H+).

Sources & evidence

ORD record
ord-05082d8316aa4aea8027b9f7d1d8f8e0
Source dataset
uspto-grants-2013_07
Patent number
US08491869B2

Reaction notes

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