Hydrogen Bromide → 660851-46-7

HRID 1827866Notes

Reaction equation

HRID 1827866 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[N:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=1)=[O:18])(C(C)(C)C)(C)C.Br.[F-].[K+].Cl>CN(C=O)C>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:16][C:17]([NH:19][C:20]2[CH:25]=[N:24][C:23]([C:26]#[N:27])=[CH:22][N:21]=2)=[O:18])[CH:11]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 522689Potassium FluorideHCID 69592227HCID 69592227, compound

Product 1

HCID 135724449660851-46-7Yield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 1E (1.66 g, 4.1 mmol) in DMF (25 mL) at room temperature was treated sequentially with 48% wt HBr (0.1 mL) and KF (0.48 g, 8.2 mmol). The mixture was stirred for 30 minutes, poured into 1N aqueous HCl (100 mL), and extracted with ethyl acetate (3×80 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes to provide 0.97 g (82.2%) of the desired product. MS (ESI(−)) m/z 288 (M−H)−; 1H NMR (500 MHz, DMSO-d6) δ 10.69 (br s, 1H), 10.48 (br s, 1H), 9.64 (s, 1H), 9.13 (d, J=1.3 Hz, 1H), 8.86 (d, J=1.3 Hz, 1H), 8.16 (d, J=2.4 Hz, 1H), 6.93 (dd, J=8.5 and 2.4 Hz, 1H), 6.87 (d, J=8.5 Hz, 1H).

Workup

  1. extractionextracted with ethyl acetate (3×80 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 60% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1b70a95821644fdea35f9a84b49c244a
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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