Potassium Phosphate, Tribasic → HCID 53373964, compound

HRID 335818Notes

Reaction equation

HRID 335818 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]=2[CH:3]=1)=[CH:13][C:12](B1OC(C)(C)C(C)(C)O1)=[CH:11][CH:10]=3.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[F:38][C:39]1[C:44](I)=[C:43]([F:46])[CH:42]=[CH:41][N:40]=1>O1CCOCC1.O.CCOC(C)=O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:38][C:39]1[C:44]([C:12]2[CH:13]=[C:14]3[C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]4[CH:3]=[C:2]([C:15]5[CH2:14][CH2:9][O:8][CH2:5][CH:4]=5)[N:7]=[CH:6][C:5]=4[O:8][C:9]3=[CH:10][CH:11]=2)=[C:43]([F:46])[CH:42]=[CH:41][N:40]=1

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 121758042,4-DIFLUORO-3-IODOPYRIDINEHCID 86658464HCID 86658464, compound

Product 1

HCID 53373964HCID 53373964, compound

Reagents, catalysts & solvents 4

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A 20 mL glass microwave reaction vessel was charged with (S)-3-chloro-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.251 g, 0.608 mmol), potassium phosphate (0.269 g, 1.266 mmol), 2,4-difluoro-3-iodopyridine (0.122 g, 0.506 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (0.036 g, 0.051 mmol) in dioxane (3.2 mL) and water (0.8 mL). The reaction mixture was heated at 100° C. for 30 min in microwave reactor. After cooling the rt the mixture was diluted with EtOAc and water. The aqueous layer was washed twice with saturated Na2CO3. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel chromatography (2-10% MeOH—CH2Cl2) to provide the desired product as a brown residue.

Workup

  1. temperatureAfter cooling the rt the mixture
  2. washThe aqueous layer was washed twice with saturated Na2CO3
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica gel chromatography (2-10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-41255c7fc8d446d6a8c584bccf1d945d
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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