Potassium Phosphate, Tribasic → US8975415, RP53b

HRID 594905Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[O:16][CH2:15][C:11]1([CH2:14][O:13][CH2:12]1)[C:5]12[CH2:9][O:8][C:7]([NH2:10])=[N:6]1.[C:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1(/C=C/C(=O)/C=C/C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:20]([C:23]1[CH:24]=[C:25]([C:2]2[CH:3]=[C:4]3[C:17](=[CH:18][CH:19]=2)[O:16][CH2:15][C:11]2([CH2:14][O:13][CH2:12]2)[C:5]23[CH2:9][O:8][C:7]([NH2:10])=[N:6]2)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22]

Participants

Conditions

Temperature: 110 °C

Procedure

The mixture of 6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (650 mg, 2.00 mmol), [5-(prop-1-yn-1-yl)pyridin-3-yl]boronic acid (644 mg, 4.00 mmol), (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one-palladium (3:2) (92 mg, 0.10 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (164 mg, 0.400 mmol), and K3PO4 (1.70 g, 8.00 mmol) in DMF (13 mL) was stirred for 16 hours at 110° C. under argon atmosphere. The precipitate formed was removed by filtration with celite and washed with CHCl3. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5) to give 6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (310 mg).

Workup

customThe precipitate formed
customwas removed by filtration with celite
washwashed with CHCl3
concentrationThe filtrate was concentrated in vacuo
customThe residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5)

Sources & evidence

ORD record: ord-a8358e7f9fdd49e48cd37310ced664ad
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242973B2

Reaction notes

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