Cesium fluoride → 4-(6-Amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)phenol

HRID 908441Notes

Reaction equation

[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[O:3][C:2]=1[C:10]1[C:11]([NH2:27])=[N:12][CH:13]=[C:14]([C:16]2[CH:17]=NN(C3CCNCC3)[CH:20]=2)[CH:15]=1.[CH3:28][C:29]1(C)[C:33](C)(C)OB(C2C=CC(O)=CC=2)[O:30]1.[F-].[Cs+]>CO.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:27][C:11]1[N:12]=[CH:13][C:14]([C:16]2[CH:20]=[CH:33][C:29]([OH:30])=[CH:28][CH:17]=2)=[CH:15][C:10]=1[C:2]1[O:3][C:4]2[C:9]([N:1]=1)=[CH:8][CH:7]=[CH:6][N:5]=2

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-bromo-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine (1 g, Example 9 starting material), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.794 g), bis(triphenylphosphine) palladium(II) chloride (0.121 g) and caesium fluoride (1.56 g) in methanol (17 ml) was heated at 120° C. for 20 min in a microwave oven. The reaction was repeated and the reaction mixtures were combined. The resulting mixture was concentrated, then diluted with water (400 ml) and stirred for 30 min. The resulting solid was filtered, washed with water (4×150 ml), dried, washed with diethyl ether (4×150 ml) and dried overnight to give 4-(6-amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)phenol (12.3 g) as a solid. NMR Spectrum: (DMSOd6) 6.88 (d, 2H), 7.50-7.57 (m, 3H), 7.72 (bs, 2H), 8.28 (dd, 1H), 8.37-8.42 (m, 2H), 8.53 (d, 1H), 8.55 (bs, 1H); Mass spectrum: M+H+ 355

Workup

customthe reaction mixtures
concentrationThe resulting mixture was concentrated
additiondiluted with water (400 ml)
filtrationThe resulting solid was filtered
washwashed with water (4×150 ml)
customdried
washwashed with diethyl ether (4×150 ml)
customdried overnight

Sources & evidence

ORD record: ord-ccc3d175b12b475893c8990d5f0970e6
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017611B2

Reaction notes

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