N-bromobutanimide → HCID 59140115, compound

HRID 2076180Notes

Reaction equation

HRID 2076180 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11][NH:12][CH:13]=[O:14])=[N:6][C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Si](C)(C)C)=[CH:18][C:17]=1[F:26].C1C(=O)N([Br:35])C(=O)C1>ClCCl>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH2:11][NH:12][CH:13]=[O:14])=[N:6][C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([Br:35])=[CH:18][C:17]=1[F:26]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59140138HCID 59140138, compound

Product 1

HCID 59140115HCID 59140115, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 5-fluoro-2-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-formylaminomethyl-nicotinic acid methyl ester (2.6 g, 6.6 mmol) in dichloromethane (65 mL) at −30° C. was added NBS (1.2 g, 6.6 mmol). The reaction mixture was stirred at −30° C. for 1.5 hours, and then concentrated under reduced pressure The resultant residue was taken up in ethyl acetate and this organic solution was washed with a saturated aqueous solution of sodium bicarbonate, followed by brine, dried (Na2SO4), filtered and evaporated in vacuo to afford the title compound as a brown solid (2.49 g, 95%). LCMS (method B): RT=3.79 min, [M+H]+=400/402.

Workup

  1. concentrationconcentrated under reduced pressure The resultant residue
  2. washthis organic solution was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-552f742db73041059b3bc416b2cf809f
Source dataset
uspto-grants-2011_04
Patent number
US07923456B2

Reaction notes

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