Cesium fluoride → HCID 67388520, compound

HRID 908453Notes

Reaction equation

HRID 908453 reaction equation
[F-].[Cs+].Br[C:4]1[CH:5]=[C:6]([C:11]2[O:12][C:13]3[C:18]([N:19]=2)=[CH:17][CH:16]=[CH:15][N:14]=3)[C:7]([NH2:10])=[N:8][CH:9]=1.B([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=1)(O)O>CO.O.[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>[NH2:10][C:7]1[N:8]=[CH:9][C:4]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=2)=[CH:5][C:6]=1[C:11]1[O:12][C:13]2[C:18]([N:19]=1)=[CH:17][CH:16]=[CH:15][N:14]=2

Participants

7

Reactant 3

HCID 25953Cesium fluorideHCID 3121834-Carboxyphenylboronic AcidHCID 67388954HCID 67388954, compound

Product 1

HCID 67388520HCID 67388520, compoundYield 95.5%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Bis(triphenylphosphine) palladium (II) chloride (0.121 g) and caesium fluoride (1.56 g) were added to a degassed solution of 5-bromo-3-oxazolo[5,4-b]pyridin-2-yl-pyridin-2-amine (1 g) and 4-boronobenzoic acid (0.570 g) in methanol (15 ml) under nitrogen atmosphere. The suspension was stirred at 120° C. for 20 min in a 300 W microwave reactor. The reaction mixture was then stirred at 130° C. for 20 minutes in a 300 W microwave reactor. The mixture was diluted with water (25 ml) and stirred for 30 min. The yellow suspension was filtered, washed with water (4×15 ml), washed with diethyl ether (4×15 ml) and dried overnight to give 4-(6-amino-5-oxazolo[5,4-b]pyridin-2-yl-3-pyridyl)benzoic acid (1.090 g, 95%). NMR Spectrum: (DMSOd6) 7.54 (dd, 1H), 7.89 (d, 2H), 7.95 (bs, 2H), 8.03 (d, 2H), 8.30 (dd, 1H), 8.41 (dd, 1H), 8.60 (d, 1H), 8.71 (d, 1H); Mass spectrum: M+H+ 333

Workup

  1. stirringThe reaction mixture was then stirred at 130° C. for 20 minutes in a 300 W microwave reactor
  2. stirringstirred for 30 min
  3. filtrationThe yellow suspension was filtered
  4. washwashed with water (4×15 ml)
  5. washwashed with diethyl ether (4×15 ml)
  6. customdried overnight

Sources & evidence

ORD record
ord-248f9df5678d41cfaf704b7c60f08178
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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