Pyridine → HCID 59128704, compound

HRID 1991118Notes

Reaction equation

HRID 1991118 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([N:21]3[C:29](=[O:30])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:22]3=[O:31])[CH:19]=2)[NH:14][CH:13]=1.N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:11][C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([N:21]3[C:22](=[O:31])[C:23]4[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:29]3=[O:30])[CH:19]=2)[N:14]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:13]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chloride2×HCID 591286662-(3-Bromo-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59128704HCID 59128704, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

PhSO2Cl (24 mg, 0.136 mmol) was added dropwise over a period of 3 min. to a stirred solution of 42 (31 mg, 0.090 mmol) and pyridine (11.4 mg, 0.144 mmol) in CH2Cl2. The mixture was stirred at r.t. overnight. Additional portion of PhSO2Cl (24 mg, 0.136 mmol) was added, followed by DMAP (3 mg, 0.025 mmol). After additional stirring for 1.5 h, the mixture was partitioned between saturated aqueous NaHCO3:CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic solutions were washed with brine, dried (MgSO4) and concentrated. Purification by PTLC using AcOEt:hexane=1:1 (v/v) as eluent afforded 43 as orange powder (15 mg, 35%). 1H NMR (400 MHz; CDCl3) δ 7.55 (tt, J=6.6, 1.6 Hz, 2H), 7.62 (tt, J=5.3, 2.0 Hz, 1H), 7.84 (dd, J=5.4, 3.0 Hz, 2H), 7.88 (s, 1H), 7.92 (d, J=2.3 Hz, 1H), 7.98 (dd, J=5.4, 3.0 Hz, 2H), 8.23 (dd, J=4.0, 1.3 Hz, 2H), 8.55 (d, J=1.9 Hz, 1H).

Workup

  1. stirringAfter additional stirring for 1.5 h
  2. customthe mixture was partitioned between saturated aqueous NaHCO3
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by PTLC

Sources & evidence

ORD record
ord-b08a24cb45da420c8339ef8b0dcb8459
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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