N-Iodosuccinimide → HCID 58944673, compound

HRID 222194Notes

Reaction equation

HRID 222194 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][C@H:13]3[CH2:15][C@H:16]([N:18]4[C:22]5[N:23]=[CH:24][N:25]=[C:26]([CH3:27])[C:21]=5[CH:20]=[CH:19]4)[CH2:17][C@H:12]3[CH2:11][O:10]2)=[CH:5][CH:4]=1.[I:28]N1C(=O)CCC1=O>C(Cl)Cl>[I:28][C:20]1[C:21]2[C:26]([CH3:27])=[N:25][CH:24]=[N:23][C:22]=2[N:18]([C@H:16]2[CH2:15][C@@H:13]3[O:14][CH:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[O:10][CH2:11][C@@H:12]3[CH2:17]2)[CH:19]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58944566HCID 58944566, compound

Product 1

HCID 58944673HCID 58944673, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d]-[1,3]dioxin-6-yl]-4-methyl-7H-pyrrolo[2,3-d]pyrimidine (363 mg, 0.995 mmol, as prepared in Example 1a-f) in DCM (15.0 mL) was added N-iodosuccinimide (256 mg, 1.14 mmol), and the mixture was stirred at rt overnight. Silica gel chromatography eluting with a gradient of 25 to 100% EtOAc in hexanes afforded the title compound (253 mg, 52%). LC/MS: Rt=2.03 min, ES+ 492 (AA standard).

Workup

  1. washSilica gel chromatography eluting with a gradient of 25 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-7446fd0a7f2249b69111d1c5c27cbda7
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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