Ethyl Acetate → 5-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine

HRID 1036145노트

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HRID 1036145 반응식
Br[C:2]1[C:3]([CH3:12])=[CH:4][C:5]2[O:9][C:8]([F:10])=[CH:7][C:6]=2[CH:11]=1.FC1(F)OC2C=C(C)C(C3N=C[C:26]([NH:29][C:30](=O)[C:31]4[CH:36]=[CH:35]C=CC=4F)=[N:27]C=3)=CC=2O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(=O)OCC>C(#N)C.O1CCOCC1.O>[F:10][C:8]1[O:9][C:5]2[CH:4]=[C:3]([CH3:12])[C:2]([C:31]3[CH:36]=[CH:35][C:26]([NH2:27])=[N:29][CH:30]=3)=[CH:11][C:6]=2[CH:7]=1

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 58486754N-(5-(2,2-difluoro-6-methylbenzo[d][1,3]dioxol-5-yl)pyrazin-2-yl)-2-fluorobenzamideHCID 584873945-Bromo-2-fluoro-6-methyl-benzofuran

생성물 1

HCID 584874145-(2-Fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine수율 56.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

A mixture of 5-bromo-2-fluoro-6-methyl-benzofuran (230) (78.5 mg, 0.34 mmol), 2-aminopyridine-5-boronic acid pinacol ester (11) (151 mg, 2 eq), bis(ditertbutyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (48 mg, 10% mol) and K3PO4 (145 mg, 0.69 mmol) in 2 ml ACN, 2 ml dioxane, 0.5 ml H2O was bubbled with argon before heated at 85° C. for 3 h. After cooling down to r.t., the reaction mixture was taken up in EA, washed with aq. NaHCO3 and brine. Org. phase was dried over Na2SO4, concentrated and then subjected to silica gel flash column chromatography (0-100% B, A: hexane; B: EA) to give 5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine (231) (46.8 mg, purity>95%, yield: 56.8%) as yellow solid.

후처리

  1. customwas bubbled with argon
  2. temperatureAfter cooling down to r.t.
  3. washwashed with aq. NaHCO3 and brine
  4. dry with materialphase was dried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5c6498d95658484488dfafa5f3db414d
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546403B2

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