2-Bromo-5-fluoropyridine → HCID 59282943, compound

HRID 1965847Notes

Reaction equation

HRID 1965847 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:18]=[CH:19][C:20]3[S:24][CH:23]=[N:22][C:21]=3[CH:25]=2)O1>>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:17]2[CH:18]=[CH:19][C:20]3[S:24][CH:23]=[N:22][C:21]=3[CH:25]=2)=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 27831712-Bromo-5-fluoropyridineHCID 467390305-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazole

Product 1

HCID 59282943HCID 59282943, compound

Procedure

Compound 5-(5-fluoropyridin-2-yl)benzo[d]thiazole (W208) was prepared using the general procedure for Suzuki coupling reaction between 2-bromo-5-fluoropyridine (39 mg, 0.22 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (53 mg, 0.2 mmol), as a white solid (20 mg, 43%). 1H NMR (400 MHz, CDCl3) δ 9.05 (s, 1 H), 8.65 (d, J=1.6 Hz, 1 H), 8.59 (d, J=2.8 Hz, 1 H), 8.14 (dd, J=8.4, 2.0 Hz, 1 H), 8.06 (d, J=8.4 Hz, 1 H), 7.85 (dd, J=8.8, 4.0 Hz, 1 H), 7.52 (td, J=8.4, 2.8 Hz, 1 H); MS (ESI) m/z 231 (M+H+).

Sources & evidence

ORD record
ord-68eb1e2a7249435c8bb51c63aa4ae892
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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