Sodium Carbonate → 4-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)benzaldehyde

HRID 856001ノート

反応式

HRID 856001 の反応式
Br[C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]1([C:10]2[CH:9]=[N:8][N:6]3[CH:7]=[C:2]([C:22]4[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=4)[CH:3]=[N:4][C:5]=23)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 586916046-Bromo-3-phenylpyrazolo[1,5-a]pyrimidine

生成物 1

HCID 586916004-(3-Phenylpyrazolo[1,5-a]pyrimidin-6-yl)benzaldehyde

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A deoxygenated solution of 6-bromo-3-phenylpyrazolo[1,5-a]pyrimidine (1-3, 2.00 g, 7.30 mmol, 1 equiv), 4-formylphenylboronic acid (1-4, 1.65 g, 11.0 mmol, 1.51 equiv), aqueous sodium carbonate solution (6.00 mL, 12.0 mmol, 1.64 equiv), and tetrakis(triphenylphosphine)palladium (0.420 g, 0.363 mmol, 0.0500 equiv) in dioxane (100 mL) was heated at reflux for 20 hours. The reaction mixture was partitioned between aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was suspended in methanol (100 mL) and filtered to give 4-(3-phenylpyrazolo[1,5-a]pyrimidin-6-yl)benzaldehyde (1-5) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ10.11 (s, 1H), 8.93 (d, 1H, J=2.4 Hz), 8.87 (d, 1H, J=2.2 Hz), 8.51 (s, 1H), 8.07 (m, 2H), 7.81 (br d, 2H, J=7.8 Hz), 7.49 (br t, 2H, J=7.7 Hz), 7.32 (t, 1H, J=7.5 Hz).

後処理

  1. temperatureat reflux for 20 hours
  2. customThe reaction mixture was partitioned between aqueous sodium bicarbonate solution (200 mL) and ethyl acetate (200 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-9a8193c00d3e44c5856eb872ac44c2b3
出典データセット
uspto-grants-2007_08
特許番号
US07262199B2

反応ノート

読み込み中…