Iodine → 4-(2,3-Dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-2-iodo-quinoline

HRID 457722Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[N:13]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][C:23]=2[F:32])[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:15][CH2:14]1.[I:33]I>O1CCCC1.C(OCC)(=O)C.O>[N:13]1([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[C:24]([I:33])[C:23]=2[F:32])[C:21]2[CH:20]=[CH:19][N:18]=[CH:17][C:16]=2[CH2:15][CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

Diisopropylamine (0.052 ml, 0.5 mmol) was added to a 50 ml round bottomed flask containing tetrahydrofuran 15. (5 ml) and magnetically stirred. The flask was cooled to 0° C. and butyllithium (0.146 ml, 2.5M solution in hexane, 0.5 mmol) was added drop wise. After 10 mins the contents were cooled to −78° C. and 4-(2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl)-3-fluoro-quinoline from Step A (0.100 g, 0.37 mmol) in 20 ml of tetrahydrofuran was added over 15 mins. The stirring was continued for an additional 2 hrs, after which iodine (0.086 g, 0.38 mmol) in 10 ml tetrahydrofuran was added. The reaction mixture was maintained at −78° C. for 2 hrs. Water and tetrahydrofuran (5 ml, 1:9) were added. The reaction mixture was diluted with ethyl acetate, washed with water and brine. Purification by column over silica gel gave pure title compound (0.97 g, 65%). MS (ES) 393.1 (M+H)+

Workup

temperatureAfter 10 mins the contents were cooled to −78° C.
temperatureThe reaction mixture was maintained at −78° C. for 2 hrs
washwashed with water and brine
customPurification by column over silica gel

Sources & evidence

ORD record: ord-8cba60d4953e4a7cb22fadb73003ba0d
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07189733B2

Reaction notes

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