1H-Pyrrolo(2,3-b)pyridine → 868387-59-1

HRID 2108768Notes

Reaction equation

HRID 2108768 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[N:11]=[C:12]([NH2:15])[S:13][CH:14]=2)=[CH:2]1.N1C2C(=CC=CN=2)C=[CH:17]1.[Al+3].[Cl-].[Cl-].[Cl-].BrC(C)C(Br)=O.NC(N)=S>>[CH3:17][C:14]1[S:13][C:12]([NH2:15])=[N:11][C:10]=1[C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1

Participants

6

Reactant 5

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 79047Propanoyl bromide, 2-bromo-HCID 2723790ThioureaHCID 6451240Aluminum(III) ChlorideHCID 39869190HCID 39869190, compound

Product 1

HCID 43141120868387-59-1

Procedure

The title compound was synthesized in 2 steps in a manner similar to that described for 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-ylamine, using 7-azaindole (1.0 g, 8.47 mmol), AlCl3 (3.4 g, 25.41 mmol, 3 eq),2-bromopropionylbromide (1.1 mL, 10.58 mmol) and thiourea (0.57 g, 7.5 mmol) (0.93 g, 41%, 2 steps) as a brown solid. Mass Spec.; MS 231 (M+1); 1H NMR(DMSO-d6, 500 MHz) δ 11.71 (s,1H), 8.36(dd, 1H), 8.21(dd,1H), 7.53(d,1H), 7.06(dd,1H), 6.67(brs,2H),2.31(s,3H).

Sources & evidence

ORD record
ord-edc58089a7e44d308c6519ba30016bdf
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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