Water → HCID 178509458, compound

HRID 1695668Notes

Reaction equation

Br[C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([NH:10][C@H:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][CH2:12]3)[O:8][CH2:9][C:4]=2[CH:3]=1.[C-:22]#[N:23].O>CN(C)C=O.[Pd].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.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>[C@H:11]1([NH:10][C:7]2[O:8][CH2:9][C:4]3[CH:3]=[C:2]([C:22]#[N:23])[CH:21]=[CH:20][C:5]=3[N:6]=2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 160 °C

Procedure

A stirred mixture of (6-bromo-4H-benzo[d][1,3]oxazin-2-yl)-(R)-indan-1-yl-amine (Example 32) (2.0 g, 5.83 mmol), zink cyanide (1.03 mg, 8.77 mmol) and tetrakis-(triphenylphosphine)-palladium (673 mg, 0.58 mmol) in N,N-dimethylformamide (20 ml) was heated at 160° C. for 15 min in a microwave reactor. The reaction mixture was poured into water (50 ml) and extracted with ethyl acetate (2×70 ml). The combined organic layers were washed with brine (2×20 ml), dried (magnesium sulfate) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel to yield the title compound as light yellow foam (693 mg, 41%). MS (ISN): m/e=288.2 (M−H−).

Workup

extractionextracted with ethyl acetate (2×70 ml)
washThe combined organic layers were washed with brine (2×20 ml)
dry with materialdried (magnesium sulfate)
customevaporated
customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record: ord-b23abd49f5d84afd8c9457ad2d0e3a2c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163740B2

Reaction notes

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