Iodine → HCID 19711283, compound

HRID 724988Notes

Reaction equation

HRID 724988 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][C:9]2[CH2:12][C:13]3[C:25]4[NH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[C:17]=4[C:16]4[C:26](=[O:29])[NH:27][CH2:28][C:15]=4[C:14]=3[C:8]=2[CH:7]=1)CCC.[I:38]I.OS([O-])=O.[Na+]>C(Cl)Cl>[I:38][C:6]1[CH:11]=[CH:10][C:9]2[CH2:12][C:13]3[C:25]4[NH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[C:17]=4[C:16]4[C:26](=[O:29])[NH:27][CH2:28][C:15]=4[C:14]=3[C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 19711250HCID 19711250, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19711283HCID 19711283, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-tributylstannyl-5H,6H,12H,13H-indeno[2,3-a]pyrrolo[3,4-c]carbazole-7(7H)one (Step-1) (16 mg, 0.026 mmol) in dry CH2Cl2 (4 mL) was added a solution of I2 (8 mg, 2 mL CH2Cl2) dropwise. The mixture was stirred at ambient temperature 2 h., then a solution of 10% NaHSO3 was added. After stirring for 10 min. the mixture was filtered. The solid was collected and washed with water, CH2Cl2 and dried under vacuum (100° C., 6 h) to give 6 mg (53%) of Compound I-40, 1H NMR (DMSO-d6, 300 MHz) d 4.29 (s, 2H), 4.96 (s, 2H), 7.33-7.50 (m, 3H), 7.66-7.79 (m, 2H), 8.29 (s, 1H), 8.62 (s, 1H), 8.42 (d, 1H), 12.08 (s, 1H). MS (m/e)=437 (m+1)+.

Workup

  1. stirringAfter stirring for 10 min. the mixture
  2. filtrationwas filtered
  3. customThe solid was collected
  4. washwashed with water, CH2Cl2
  5. customdried under vacuum (100° C., 6 h)

Sources & evidence

ORD record
ord-bd831907429a41d9879c0aa57a6129d3
Source dataset
uspto-grants-1998_01
Patent number
US05705511

Reaction notes

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