Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro- → Pyrano(2,3-g)indole, 1,7,8,9-tetrahydro-

HRID 1374810Notes

Reaction equation

HRID 1374810 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:13][CH2:12][CH2:11][CH2:10][C:8]3=2)[CH:3]=[C:2]1C(O)=O.[O:17]1[C:29]2[C:21]([CH2:22][C:23]3[CH2:24][CH2:25][NH:26][C:27]=3[CH:28]=2)=[CH:20][CH:19]=[C:18]1C(O)=O.O1C2C3C=CNC=3CCC=2C=CC1C(O)=O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[O:13][CH2:12][CH2:11][CH2:10][C:8]3=2)[CH:3]=[CH:2]1.[O:17]1[C:29]2[C:28]3[CH:24]=[CH:25][NH:26][C:27]=3[CH2:23][CH2:22][C:21]=2[CH:20]=[CH:19][CH2:18]1

Participants

5

Reactant 3

HCID 3067316Pyrano(2,3-g)indole-2-carboxylic acid, 1,7,8,9-tetrahydro-HCID 222827195,6-dihydro-7H-pyrano[2,3-e]indole-2-carboxylic acidHCID 866003476,7-dihydro-5H-pyrano[3,2-f]indole-2 carboxylic acid

Product 2

HCID 3067319Pyrano(2,3-g)indole, 1,7,8,9-tetrahydro-HCID 222826945,6-dihydro-7H-pyrano[2,3-e]indole

Procedure

7,8-Dihydro-9H-pyrano[2,3-g]indole, 6,7-dihydro-5H-pyrano[3,2-g]indole and 5,6-dihydro-7H-pyrano[2,3-e]indole were prepared according to the procedure described in Example 3, using a mixture [(2,3-g):(3,2-f):(2,3-e)—11:1:4] of 7,8-dihydro-9H-pyrano[2,3-g]indole-2-carboxylic acid, 6,7-dihydro-5H-pyrano[3,2-f]indole-2-carboxylic acid and 5,6-dihydro-7H-pyrano[2,3-e]indole-2-carboxylic acid (3.12 g, 14.4 mmol) to produce, after flash column chromatography (and without further separation on a second column) a mixture [(2,3-g):(2,3-e)—72:28] of products (2.01 g, 80%) as a white, crystalline solid [Rf 0.46 (SiO2; dichloromethane)] which was used without further purification. Also collected was 6,7-dihydro-5H-pyrano[3,2-f] indole (250 mg, 10%) as an off-white solid [Rf 0.33 (SiO2; dichloromethane)].

Workup

  1. customto produce
  2. customafter flash column chromatography (and without further separation on a second column) a mixture [(2,3-g):(2,3-e)—72:28] of products (2.01 g, 80%) as a white, crystalline solid [Rf 0.46 (SiO2; dichloromethane)] which
  3. customwas used without further purification
  4. customAlso collected

Sources & evidence

ORD record
ord-76df1be412bc40aab15c71fe01bd3c8e
Source dataset
uspto-grants-2007_01
Patent number
US07166613B2

Reaction notes

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