5-Bromo-2-phenyl-1,3-oxazole → 3-(2-Phenyl-oxazol-5-yl)-2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 751283Notes

Reaction equation

HRID 751283 reaction equation
Br[C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20](B(O)O)=[C:21]2[CH2:26][CH2:25][CH2:24][N:22]2[N:23]=1>>[C:7]1([C:5]2[O:6][C:2]([C:20]3[C:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][N:13]=4)=[N:23][N:22]4[CH2:24][CH2:25][CH2:26][C:21]=34)=[CH:3][N:4]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 2

HCID 27732715-Bromo-2-phenyl-1,3-oxazoleHCID 59710031(2-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid

Product 1

HCID 97974893-(2-Phenyl-oxazol-5-yl)-2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoleYield 12%

Procedure

In a similar fashion to Example 1, react 5-bromo-2-phenyloxazole (Combi-Blocks; 120 mg, 0.52 mmol) with 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 5; 120 mg, 0.52 mmol) to provide the title compound (20 mg, 12%) as a white solid. MS ESI+ m/e 329 (M+1). 1H NMR (CDCl3) δ 8.78-8.70 (m, 1H), 8.05-7.99 (m, 2H), 7.95-7.89 (m, 1H), 7.82 (s, 1H), 7.81-7.70 (m, 1H), 7.50-7.41 (m, 3H), 7.30-7.25 (m, 1H), 4.31-4.21 (m, 2H), 3.38-3.24 (m, 2H), 2.82-2.66 (m, 2H). HPLC: 97.2%, Rt=16.67 min. TLC (SiO2): Rf0.3 (1:3 [80:18:2 chloroform/methanol/concentrated aqueous ammonium hydroxide]/dichloromethane).

Sources & evidence

ORD record
ord-ed3235d05d7d44a899a87b2985f06970
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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