Water → HCID 86721473, compound

HRID 869612Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:32]=1)[O:7][CH2:8][C:9]1[CH:19]=[C:18]([CH2:20][C:21]3[N:25]4[CH:26]=[CH:27][C:28](Br)=[CH:29][C:24]4=[N:23][C:22]=3[CH3:31])[CH:17]=[CH:16][C:10]=1/[C:11]/2=[C:12](/[CH3:15])\[C:13]#[N:14].[CH:33]1(B(O)O)[CH2:35][CH2:34]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:33]1([C:28]2[CH:27]=[CH:26][N:25]3[C:21]([CH2:20][C:18]4[CH:17]=[CH:16][C:10]5/[C:11](=[C:12](/[CH3:15])\[C:13]#[N:14])/[C:5]6[CH:4]=[CH:3][C:2]([F:1])=[CH:32][C:6]=6[O:7][CH2:8][C:9]=5[CH:19]=4)=[C:22]([CH3:31])[N:23]=[C:24]3[CH:29]=2)[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 100 °C

Procedure

[step 5] (E)-2-{3-fluoro-8-[(7-bromo-2-methylimidazo[1,2-a]pyridin-3-yl)methyl]dibenzo[b,e]oxepin-11(6H)-ylidene}propanenitrile (350 mg, 0.72 mmol) obtained in step 4 was dissolved in toluene (4.0 mL), cyclopropylboronic acid (123 mg, 1.4 mmol), tricyclohexylphosphine (80 mg, 0.29 mmol), palladium acetate (32 mg, 0.14 mmol), potassium phosphate (532 mg, 2.5 mmol) and water (13 mg, 0.72 mmol) were added, and the mixture was stirred with heating at 100° C. for 3 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=19/1 v/v) to give the title compound (280 mg, 87%).

Workup

filtrationThe reaction mixture was filtered through celite
concentrationthe filtrate was concentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=19/1 v/v)

Sources & evidence

ORD record: ord-12c6784bfdec424eb74278368d641c46
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969345B2

Reaction notes

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