4-Toluenesulfonyl chloride → tert-butyl 4-(2-fluoro-4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

HRID 531457Notes

Reaction equation

HRID 531457 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.[F:22][C:23]1[CH:28]=[C:27](C2C=C3C(I)=CNC3=NC=2)[CH:26]=[CH:25][C:24]=1[CH:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:22][C:23]1[CH:28]=[C:27]([C:2]2[CH:3]=[C:4]3[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]4[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=4)(=[O:14])=[O:13])[C:5]3=[N:6][CH:7]=2)[CH:26]=[CH:25][C:24]=1[CH:39]1[CH2:44][CH2:43][N:42]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:41][CH2:40]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 118524041tert-butyl 4-(2-fluoro-4-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate

Product 1

HCID 90033965tert-butyl 4-(2-fluoro-4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylateYield 48.26%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Using similar reaction conditions as described in, step ii of Intermediate 1, tert-butyl 4-(2-fluoro-4-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperidine-1-carboxylate (400 mg, 0.767 mmol) was tosylated with p-toluene sulfonylchloride (220 mg, 1.151 mmol) and DMAP (282 mg, 2.303 mmol) in DCM (20 mL) to afford 250 mg (48.26% yield) of the titled compound after purification with (60/120 silica gel) column chromatography using 1% methanol in DCM as eluent. MS: m/z=676.3 (M+1). 1H NMR (CDCl3, 300 MHz): δ 8.619-8.611 (d, 1H), 8.12-8.09 (d, 2H), 7.89 (s, 1H), 7.767-7.760 (d, 1H), 7.31-7.23 (m, 5H), 4.26 (s, 2H), 3.08-3.00 (m, 1H), 2.95-2.75 (m, 2H), 2.38 (s, 3H), 1.86-1.64 (m, 4H), 1.489 (s, 9H).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-4134af7c19904473833d139871cd10bc
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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