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

HRID 856001노트

반응식

HRID 856001 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9a8193c00d3e44c5856eb872ac44c2b3
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262199B2

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