Benzyl Bromide → HCID 11857729, compound

HRID 1993392Notes

Reaction equation

HRID 1993392 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[C:30](=[O:31])[CH2:29][NH:28][C:27]4=[O:32])=[CH:22][C:21]=3[F:33])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:34][CH3:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1.CN(C=O)C>[CH2:36]([N:28]1[CH2:29][C:30](=[O:31])[N:26]([C:23]2[CH:24]=[CH:25][C:20]([O:19][C:13]3[C:12]4[C:17](=[CH:18][C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[C:10]([O:34][CH3:35])[CH:11]=4)[N:16]=[CH:15][CH:14]=3)=[C:21]([F:33])[CH:22]=2)[C:27]1=[O:32])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 2733832Lithium HexamethyldisilazideHCID 59134428HCID 59134428, compound

Product 1

HCID 11857729HCID 11857729, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring suspension of 3-(4-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3-fluorophenyl)imidazolidine-2,4-dione (Example 50, 200 mg, 0.42 mmol) and benzyl bromide (0.06 mL, 0.51 mmol) in THF (2 mL) and DMF (1 mL) was added 1 M LiHMDS in THF (0.51 mL). After 3 h at RT, the solvents were removed under reduced pressure and the residue was purified on a silica gel to afford the title compound. Calc'd Mass for C33H26FN3O5, 563, MS (M+1) 564.

Workup

  1. customthe solvents were removed under reduced pressure
  2. customthe residue was purified on a silica gel

Sources & evidence

ORD record
ord-96e0a76f40ee448ba2de97a2f6a3645f
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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