Trimethylsilyldiazomethane → HCID 68828891, compound

HRID 658394Notes

Reaction equation

HRID 658394 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[CH:17]=[N:16][CH:15]=[C:14]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:10]=1[C:11]([OH:13])=[O:12]>C1COCC1.CO>[CH3:1][O:12][C:11](=[O:13])[C:10]1[C:14]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])=[CH:15][N:16]=[CH:17][C:9]=1[Br:8].[Br:8][C:9]1[CH:17]=[N:16][CH:15]=[C:14]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[C:10]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 59026788HCID 59026788, compound

Product 1

HCID 68828891HCID 68828891, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(Trimethylsilyl)diazomethane (8.1 mL, 2M in THF, 16.2 mmol) was added to a solution of 3-bromo-5-(2-fluoro-phenylamino)-isonicotinic acid (4.2 g, 13.5 mmol) in THF/MeOH (72 mL, 9/1, v/v) and stirred for 2 h at room temperature. The reaction solution was quenched with acetic acid, and then concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 50% EtOAc in hexanes to afford the desired product (4.1 g, 94%) as a yellow solid.

Workup

  1. customThe reaction solution was quenched with acetic acid
  2. concentrationconcentrated
  3. customThe crude product was purified via Biotage
  4. washeluting with a gradient of 0 to 50% EtOAc in hexanes

Sources & evidence

ORD record
ord-7619a98f159c4fa8a3e58348e5c92119
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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