Benzyl mercaptan → HCID 90111076, compound

HRID 1051406Notes

Reaction equation

HRID 1051406 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][N:6]=[CH:5]2.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CCN(C(C)C)C(C)C.[CH2:63]([SH:70])[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>O1CCOCC1.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]>[CH2:63]([S:70][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][N:6]=[CH:5]2)[C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 468639235-Bromo-6-fluoro-1H-indazole

Product 1

HCID 90111076HCID 90111076, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 5-bromo-6-fluoro-1H-indazole (1-1, 1.0 g, 5.08 mmol, 1.0 equiv), Xantphos (0.294 g, 0.508 mmol, 0.1 equiv), and Pd2(dba)3 (0.465 g, 0.508 mmol, 0.1 equiv) was made in dioxane (25 mL) followed by the addition of DIEA (1.77 mL, 10.15 mmol, 2.0 equiv) and benzylmercaptan (0.630 mL, 5.33 mmol, 1.05 equiv) and the reaction was stirred at 120° C. overnight. The reaction mixture concentrated in vacuo and purified using normal phase chromatography. ESI+ MS [M+H]+ C14H11FN2S: 259.9 found, 259.3 required.

Workup

  1. concentrationThe reaction mixture concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-0ee2714024f140088896ad796c9ec1e1
Source dataset
uspto-grants-2016_07
Patent number
US09388179B2

Reaction notes

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