Ethyl formate → Methyl 9-bromo-10-fluoro-3-formyl-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxylate

HRID 575134Notes

Reaction equation

HRID 575134 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][C:15]=1[F:16])[CH:12]1[CH2:17][CH:10]([CH2:11]1)[N:9]1[C:5]2=[N:6][C:7]([C:18]([O:20][CH3:21])=[O:19])=[CH:8]1.[CH:22](OCC)=[O:23]>O>[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:13]2[CH:12]3[CH2:11][CH:10]([CH2:17]3)[N:9]3[C:5](=[N:6][C:7]([C:18]([O:20][CH3:21])=[O:19])=[C:8]3[CH:22]=[O:23])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 86693079Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Product 1

HCID 86693159Methyl 9-bromo-10-fluoro-3-formyl-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 9-bromo-10-fluoro-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7,9,11-pentaene-4-carboxylate (4 g) was reacted with ethyl formate similar to as described in Example 8 or Example 9 to give (2.3 g) of methyl 9-bromo-10-fluoro-3-formyl-2,5-diazatetracyclo[11.1.1.0[2,6].0[7,12]]pentadeca-3,5,7(12),8,10-pentaene-4-carboxylate following triteration from water.

Sources & evidence

ORD record
ord-ca40143a91784adeb9030534179e084b
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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