Tributylphosphine → HCID 118415304, compound

HRID 1051414Notes

Reaction equation

HRID 1051414 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[CH3:19])[NH:15][N:14]=[CH:13]2)(=[O:9])=[O:8].CCCCP(CCCC)CCCC.O[C@H:47]([C:49]1[CH:50]=[CH:51][CH:52]=[C:53]2[C:58]=1[CH2:57][N:56]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:55][CH2:54]2)[CH3:48]>C1COCC1>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[N:21]=1)[S:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:18]=1[CH3:19])[N:15]([C@@H:47]([C:49]1[CH:50]=[CH:51][CH:52]=[C:53]3[C:58]=1[CH2:57][N:56]([C:59]([O:61][C:62]([CH3:63])([CH3:65])[CH3:64])=[O:60])[CH2:55][CH2:54]3)[CH3:48])[N:14]=[CH:13]2)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 13831TributylphosphineHCID 89533737HCID 89533737, compoundHCID 90110410HCID 90110410, compound

Product 1

HCID 118415304HCID 118415304, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL RB flask containing THF (4381 μl) at 0° C. was added sequentially N-(2,4-dimethoxybenzyl)-N-(6-fluoropyridin-2-yl)-6-methyl-1H-indazole-5-sulfonamide (4-5, 200 mg, 0.438 mmol), TRI-N-BUTYLPHOSPHINE (216 μl, 0.876 mmol), DTBAD (202 mg, 0.876 mmol) and (S)-tert-butyl 8-(1-hydroxyethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (243 mg, 0.876 mmol). After 50 min at 0° C., concentrated in vacuo. Purified by normal-phase ISCO (40 g column, 0-40% EtOAc:Hex) to give an off-white solid

Workup

  1. concentrationconcentrated in vacuo
  2. customPurified by normal-phase ISCO (40 g column, 0-40% EtOAc:Hex)
  3. customto give an off-white solid

Sources & evidence

ORD record
ord-93b49392322d4ba088e819d339580977
Source dataset
uspto-grants-2016_07
Patent number
US09388179B2

Reaction notes

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