Potassium Phosphate, Tribasic → US8975415, RP53b

HRID 594905ノート

反応式

HRID 594905 の反応式
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]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 574164825-(1-Propynyl)pyridine-3-boronic Acid (contains varying amounts of Anhydride)HCID 867243126'-Bromodispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-amine

生成物 1

HCID 86724311US8975415, RP53b収率 42.9%

試薬・触媒・溶媒 2

HCID 15673654(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-a8358e7f9fdd49e48cd37310ced664ad
出典データセット
uspto-grants-2016_01
特許番号
US09242973B2

反応ノート

読み込み中…