N-bromobutanimide → HCID 58929010, compound

HRID 853614Notes

Reaction equation

HRID 853614 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([N:11]3[C:23](=[O:24])[C:22]4[C:13](=[N:14][C:15]5[C:20]([C:21]=4[O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[N:19][CH:18]=[CH:17][C:16]=5[CH3:36])[C:12]3=[O:37])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br:38]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:38][CH2:36][C:16]1[CH:17]=[CH:18][N:19]=[C:20]2[C:15]=1[N:14]=[C:13]1[C:12](=[O:37])[N:11]([C:8]3([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:10][CH2:9]3)[C:23](=[O:24])[C:22]1=[C:21]2[O:25][Si:26]([CH:30]([CH3:31])[CH3:32])([CH:33]([CH3:35])[CH3:34])[CH:27]([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58929031HCID 58929031, compound

Product 1

HCID 58929010HCID 58929010, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

As a further example, 7-[1-(4-fluoro-phenyl)-cyclopropyl]-4-methyl-9-triisopropylsilanyloxy-pyrrolo[3,4-b][1,5]naphthyridine-6,8-dione A20.17, prepared according to the procedures described above, is reacted with N-bromosuccinimide in refluxing ethyl acetate to give 4-bromomethyl-7-[1-(4-fluoro-phenyl)-cyclopropyl]-9-triisopropylsilanyloxy-pyrrolo[3,4-b][1,5]naphthyridine-6,8-dione A20.18. The product is then heated at 120° C. with excess of a trialkyl phosphite to give after deprotection the phosphonate A20.19.

Sources & evidence

ORD record
ord-6b8bb149857744eb8d7d26f6c504e5c6
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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