Potassium Phosphate, Tribasic → HCID 53464944, compound

HRID 335922Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([F:8])[C:5]2[O:9][C:10]3[C:15]([C@@:16]4([CH2:20][O:19][C:18]([NH2:21])=[N:17]4)[C:4]=2[CH:3]=1)=[CH:14][C:13]([C:22]1[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=1)=[CH:12][CH:11]=3.[O:29]1[CH2:34][CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH2:31][CH2:30]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[O:29]1[CH2:30][CH:31]=[C:32]([C:2]2[N:7]=[C:6]([F:8])[C:5]3[O:9][C:10]4[C:15]([C@@:16]5([CH2:20][O:19][C:18]([NH2:21])=[N:17]5)[C:4]=3[CH:3]=2)=[CH:14][C:13]([C:22]2[C:23]([F:28])=[N:24][CH:25]=[CH:26][CH:27]=2)=[CH:12][CH:11]=4)[CH2:33][CH2:34]1

Participants

Conditions

Temperature: 135 °C

Procedure

A reaction vessel charged with (S)-3-chloro-1-fluoro-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (95 mg, 0.237 mmol; prepared as described in Method BB33) 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100 mg, 0.474 mmol), bis-(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (8.39 mg, 0.012 mmol) and potassium phosphate (111 mg, 0.522 mmol) in 1.5 ml of a 2:1 mixture of dioxane and was heated at 135° C. microwave for 25 minutes. The reaction mixture was loaded directly onto a silica gel column and purified (CH2Cl2 to CH2Cl2/ethyl acetate=3:1 to 2:1 to 1:1 to 100% ethyl acetate to ethyl acetate/MeOH=100:5) to provide (S)-3-(3,6-dihydro-2H-pyran-4-yl)-1-fluoro-7-(2-fluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine as a off-white solid. MS m/z=449.0 [M+H]+. Calculated for C24H18F2N4O3: 448.42.

Workup

custompurified (CH2Cl2 to CH2Cl2/ethyl acetate=3:1 to 2:1 to 1:1 to 100% ethyl acetate to ethyl acetate/MeOH=100:5)

Sources & evidence

ORD record: ord-2dfe0f06030d433e916b8cfd3ea0f91d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Reaction notes

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