Chlorosuccinimide → 1-(4-Bromo-3-fluorophenyl)propan-1-one

HRID 561981Notes

Reaction equation

HRID 561981 reaction equation
I[C:2]1C=CC(C2NC([C@@H](N3C(=O)[C@@H](CCC(O)=O)NC3=O)C(C)C)=NC=2)=C[CH:3]=1.C(OC(=O)N[C@H](C1NC(C2C=CC=CC=2F)=CN=1)[C@H](C1C=CC=CC=1)C)(C)(C)C.C(OC(N[C@H](C1C=CC(OCC(=O)N(C)C)=CC=1)C(O)=O)=O)(C)(C)C.ClN1C(=O)CCC1=O.BrC1C=CC(C(=O)C)=C(Cl)C=1.[Br:102][C:103]1[CH:111]=[CH:110][C:106]([C:107]([OH:109])=O)=[CH:105][C:104]=1[F:112]>>[Br:102][C:103]1[CH:111]=[CH:110][C:106]([C:107](=[O:109])[CH2:2][CH3:3])=[CH:105][C:104]=1[F:112]

Participants

7

Reactant 6

HCID 31398ChlorosuccinimideHCID 27733414-Bromo-3-fluorobenzoic acidHCID 155609501-(4-Bromo-2-chlorophenyl)ethan-1-oneHCID 577719783-((R)-1-{(S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-methyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-propionic acidHCID 66815126(R)-tert-butoxycarbonylamino-(4-dimethylcarbamoylmethoxy-phenyl)-acetic acid2×HCID 67001749{(1S,2S)-1-[5-(2-fluoro-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 242120871-(4-Bromo-3-fluorophenyl)propan-1-one

Procedure

Prepared by the same method as described in example 1 except that (i) steps A, B and C were omitted; (ii) 1-(4-bromo-3-fluoro-phenyl)-propan-1-one was used in place of 1-(2-fluoro-4-iodo-phenyl)-ethanone in step 21-D; (iii) (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid in step 21-E; and (iv) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 21-F was omitted. 1-(4-Bromo-3-fluoro-phenyl)-propan-1-one was prepared as described in example 6 for the preparation of 1-(4-bromo-2-chloro-phenyl)-ethanone except that 4-bromo-3-fluorobenzoic acid was used in place of 4-bromo-2-chlorobenzoic acid in step 21-I. HR-MS: calcd for C28H24BrFN4O4 [M+H+] 579.1038. Found 579.1038.

Workup

  1. customPrepared by the same method

Sources & evidence

ORD record
ord-eef49124d92f4b308d774c2a9447ce57
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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