Tributylphosphine → HCID 71515892, compound

HRID 574641Notes

Reaction equation

HRID 574641 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16][C:11]=3[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.[C@@H:51]1(O)[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:53][CH2:52]1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]3[CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16][C:11]=3[N:10]([C@H:51]3[C:59]4[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=4)[CH2:53][CH2:52]3)[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 6971242(S)-(+)-1-IndanolHCID 57076369HCID 57076369, compound

Product 1

HCID 71515892HCID 71515892, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

According to Scheme 7: A mixture of 1-[3-(4-fluoro-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone (3b) (0.2 g, 0.771 mmol), tri-n-butylphosphine (0.312 g, 1.54 mmol), 1,1′-(azodicarbonyl)dipiperidine (0.389 g, 1.54 mmol) and (S)-1-indanol in dry toluene (2.5 ml) was stirred at 80° C. for 2 h. Solvents were evaporated in vacuo. The crude product was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 81 mg of 1-[(R)-3-(4-fluoro-phenyl)-1-indan-1-yl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone (12a)

Workup

  1. customSolvents were evaporated in vacuo
  2. customThe crude product was purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-bf78d23c252b4bec8f81c3ddac118741
Source dataset
uspto-grants-2015_05
Patent number
US09034897B2

Reaction notes

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