Tributylvinyltin → HCID 86643484, compound

HRID 1423371Notes

Reaction equation

HRID 1423371 reaction equation
Br[C:2]1[C:15]([O:16][CH3:17])=[CH:14][C:13]2[C:4](=[C:5]([O:20][C@H:21]3[CH2:25][N:24]([C:26](=[O:44])[C@H:27]([CH:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)[NH:28][C:29]([O:31][CH2:32][C:33]([CH3:38])([CH3:37])[CH2:34][CH:35]=[CH2:36])=[O:30])[C@H:23]([C:45]([O:47][CH3:48])=[O:46])[CH2:22]3)[N:6]=[C:7]3[C:12]=2[CH:11]=[CH:10][C:9]([C:18]#[N:19])=[CH:8]3)[CH:3]=1.[CH:49]([Sn](CCCC)(CCCC)CCCC)=[CH2:50]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:7]([CH:8]=1)=[N:6][C:5]([O:20][C@H:21]1[CH2:25][N:24]([C:26](=[O:44])[C@H:27]([CH:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[NH:28][C:29]([O:31][CH2:32][C:33]([CH3:37])([CH3:38])[CH2:34][CH:35]=[CH2:36])=[O:30])[C@H:23]([C:45]([O:47][CH3:48])=[O:46])[CH2:22]1)=[C:4]1[C:13]=2[CH:14]=[C:15]([O:16][CH3:17])[C:2]([CH:49]=[CH2:50])=[CH:3]1)#[N:19]

Participants

5

Reactant 2

HCID 81998TributylvinyltinHCID 59408870HCID 59408870, compound2×

Product 1

HCID 86643484HCID 86643484, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a degassed solution of the product mixture from Step 2, methyl (4R)-4-[(8-bromo-3-cyano-9-methoxyphenanthridin-6-yl)oxy]-1-[(2S)-2-cyclopentyl-2-({[(2,2-dimethylpent-4-en-1-yl)oxy]carbonyl}amino)acetyl]-L-prolinate (420 mg, 0.58 mmol) in PhMe (10 mL) was added vinyltributyltin (0.205 mL, 0.70 mmol) and tetrakis(triphenylphosphine)palladium (67 mg, 0.06 mmol). The mixture was then heated to reflux for 18 h. The solvent was then removed in vacuo and the crude material was purified on silica (gradient elution, 10-50% EtOAc/hex) to provide the title compound. LRMS (M+H)+=669.3.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 18 h
  3. customThe solvent was then removed in vacuo
  4. customthe crude material was purified on silica (gradient elution, 10-50% EtOAc/hex)

Sources & evidence

ORD record
ord-e2d13a50a7fe44d58a6a8e1545243770
Source dataset
uspto-grants-2015_01
Patent number
US08927569B2

Reaction notes

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