Sodium Iodide → 3-[2'-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-5'-iodo-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]-diazepin-2-one

HRID 74610Notes

Reaction equation

[I-:1].[Na+].Br[C:4]1[C:5]([N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[CH2:34][CH2:33][C:32]4[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:31]=4[NH:30][C:29]3=[O:41])[CH2:24][CH2:23]2)=[CH:6][C:7]([C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[O:11])=[N:8][CH:9]=1.CN(C=O)C>O1CCOCC1.O.[Cu](I)I>[F:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([C:10]([C:7]1[CH:6]=[C:5]([N:22]3[CH2:27][CH2:26][CH:25]([N:28]4[CH2:34][CH2:33][C:32]5[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:31]=5[NH:30][C:29]4=[O:41])[CH2:24][CH2:23]3)[C:4]([I:1])=[CH:9][N:8]=1)=[O:11])[CH2:13][CH2:14]2

Participants

Conditions

Temperature: 110 °C

Procedure

Under a nitrogen atmosphere 91 mg (0.61 mmol) sodium-iodide, 6 mg (0.03 mmol) copper iodide and 0.09 mL (0.01 mmol) N,N-dimethylene-ethylene-diamine were added to 0.18 g (0.30 mmol) 3-[5′-bromo-2′-(5-fluoro-2,3-dihydro-indole-1-carbonyl)-3,4,5,6-tetrahydro-2H-[1,4′]bipyridinyl-4-yl]-7-methoxy-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one in 1.0 mL 1,4-dioxane and the mixture was stirred overnight at 110° C. Then an additional 0.3 mL DMF was added and the reaction mixture was stirred for a further 10 days at 110° C. After being diluted with water the precipitate formed was suction filtered and dried.

Workup

stirringthe reaction mixture was stirred for a further 10 days at 110° C
customformed
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-7ae36b8265044f15b31fdb65330fa012
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829006B2

Reaction notes

Loading…