1-Hydroxy-2,1-benzoxaborole → 9-hydroxy-4-[2-(hydroxymethyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11028Notes

Reaction equation

HRID 11028 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8](I)[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1.B1(O)[O:29][CH2:28][C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2>C1COCC1.C(Cl)Cl.CCCCCC>[OH:1][C:2]1[CH:14]=[CH:13][C:12]2[NH:11][C:10]3[CH:9]=[C:8]([C:26]4[CH:25]=[CH:24][CH:23]=[CH:22][C:27]=4[CH2:28][OH:29])[C:7]4[C:16](=[O:20])[NH:17][C:18](=[O:19])[C:6]=4[C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4037881-Hydroxy-2,1-benzoxaboroleHCID 118428349-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 118429999-hydroxy-4-[2-(hydroxymethyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 57%

Reagents, catalysts & solvents 1

HCID 19387301HCID 19387301, compoundSolvent

Procedure

The reaction of 9-hydroxy-4-iodopyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione, prepared as in example 7, with 2-(hydroxymethyl)benzeneboronic acid cyclic monoester according to the procedure described in example 8 gave 9-Hydroxy-4-[2-(hydroxymethyl)phenyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (503) (I; Ar=2-(hydroxymethyl)phenyl) in a 57% yield, mp (THF/CH2Cl2/hexane) 270–280° C. (dec). 1H NMR [(CD3)2SO] δ 11.76 (br s, 1H), 10.96 (br s, 1H), 9.25 (br s, 1H), 8.32 (d, J=2.4 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.47 (s, 1H), 7.44 (d, J=8.5 Hz, 1H), 7.43 (td, J=7.6, 1.2 Hz, 1H), 7.31 (td, J=7.4, 0.9 Hz, 1H), 7.23 (dd, J=7.5, 1.0 Hz, 1H), 7.06 (dd, J=8.7, 2.5 Hz, 1H), 5.00 (t, J=5.4 Hz, 1H), 4.33 (dd, J=13.6, 5.2 Hz, 1H), 4.24 (dd, J=13.5, 5.3 Hz, 1H). Found: C, 68.41; H, 4.29; N, 7.59. C21H14N2O4,1/2H2O requires C, 68.66; H, 4.12; N, 7.63.

Sources & evidence

ORD record
ord-393318a5d3624563b2558d3147430d5f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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