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Triethylamine → 3-[(5-cyclopropyl-1-phenyl-1H-pyrazol-4-yl)ethynyl]-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

HRID 1253484
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HRID 1253484 반응식
[C:1]([C:3]1[CH:4]=[N:5][N:6]2[CH:11]=[C:10]([C:12]3[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=3)[CH:9]=[C:8]([O:18][CH3:19])[C:7]=12)#[CH:2].[CH:20]1([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][C:24]=2I)[CH2:22][CH2:21]1.C(N(CC)CC)C>CN(C)C=O.[Cu]I.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:20]1([C:23]2[N:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:26]=[CH:25][C:24]=2[C:2]#[C:1][C:3]2[CH:4]=[N:5][N:6]3[CH:11]=[C:10]([C:12]4[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=4)[CH:9]=[C:8]([O:18][CH3:19])[C:7]=23)[CH2:22][CH2:21]1
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참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 584046903-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridineHCID 672072835-cyclopropyl-4-iodo-1-phenyl-1H-pyrazole

생성물 1

HCID 584047073-[(5-cyclopropyl-1-phenyl-1H-pyrazol-4-yl)ethynyl]-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

To a mixture of 3-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (40 mg, 0.160 mmol), 5-cyclopropyl-4-iodo-1-phenyl-1H-pyrazole (62 mg, 0.20 mmol), copper (I) iodide (9.1 mg, 0.048 mmol), and tetrakis(triphenylphosphine)palladium (0) (18.3 mg, 0.016 mmol) in N,N-dimethylformamide (2 ml), was added triethylamine (0.044 ml, 0.32 mmol). The mixture was sparged with argon for 3 minutes and heated to 70° C. After 1 h, reaction mixture was purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 3-[(5-cyclopropyl-1-phenyl-1H-pyrazol-4-yl)ethynyl]-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine.

후처리

  1. customThe mixture was sparged with argon for 3 minutes
  2. customreaction mixture
  3. customwas purified directly by preparative HPLC Reverse phase (C-18)
  4. washeluting with acetonitrile/water+0.05% TFA

출처 및 근거

ORD 기록
ord-5490aa2c2b2d442fb1f1b206ca0bda0b
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08455477B2

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